South Chesapeake Homes with Well Exterior features

Welcome to South Chesapeake, Virginia, a hidden gem nestled in the heart of Chesapeake County. This vibrant community seamlessly blends the charm of suburban living with the convenience of urban amenities. South Chesapeake boasts a rich tapestry of parks, recreational facilities, and scenic waterways, making it a perfect destination for families, outdoor enthusiasts, and anyone looking to enjoy a balanced lifestyle.

One of the standout features of homes in South Chesapeake is their well-designed exteriors. Many properties showcase stunning curb appeal, with beautifully landscaped yards, inviting porches, and a variety of architectural styles that reflect the area’s unique character. Whether you’re drawn to classic Colonial designs or modern craftsman aesthetics, you’ll find homes that not only meet your needs but also enhance the neighborhood’s charm.

The community is known for its strong sense of belonging, with friendly neighbors and numerous local events that foster connections among residents. Families will appreciate the top-rated schools and safe streets, while nature lovers can explore the nearby parks and trails, perfect for weekend adventures or leisurely strolls.

With a growing selection of shops, restaurants, and entertainment options just a short drive away, South Chesapeake offers the best of both worlds: a serene residential environment coupled with easy access to urban conveniences. Discover your dream home in South Chesapeake today, where the perfect blend of comfort, style, and community awaits you!

Newest South Chesapeake Homes with Well Exterior features

$649,900

4 Beds ⋅ 3.1 Baths ⋅ 10655286 MLS

Welcome to your very own homesteader’s haven in the heart of Chesapeake! Tucked away on over an acre, this one-of-a-kind brick ranch offers a blend of modern comfort and timeless, back-to-the-land charm. Outside, you'll be greeted by a flourishing orchard with established fruit trees that provide a bounty through every season, blueberries, figs and plums for jam-making, crisp apples, cherries, peaches, pomegranates, and pecans for baking. Designed for self-sufficiency with two outbuildings, a 40’x45’ parking area ideal for your boat or RV, solar panels and a new roof provide energy savings. The fully finished converted garage for an in-law suite, playroom, fifth bedroom, business front, the choice is yours. If you’re dreaming of tending gardens and evenings under the trees enjoying the fruits of your own land, this property has it all. A true little piece of paradise, right in the city yet worlds away.

101 Stadium Drive, South Chesapeake

$975,000

6 Beds ⋅ 3.1 Baths ⋅ 10655175 MLS

Discover a private country retreat in the heart of Grassfield, where approximately 5 tree-lined acres create a peaceful setting rarely found with this much space and convenience. Over 4,000 sqft of living space with 6 beds, 3.5 baths, first floor primary ensuite. Spend summer days by the pool, unwind beneath the stars in the hot tub, or enjoy the freedom of acreage with a barn and zoning that permits horses. Mature trees frame the property and provide a sense of privacy while still placing you in the heart of Chesapeake, convenient to shopping, dining, schools and major routes.

2536 Seven Eleven Road, South Chesapeake

$1,300,000

4 Beds ⋅ 2.1 Baths ⋅ 10654856 MLS

Elegant custom details and room to live the life you’ve imagined! Sweeping down a long, paved driveway, this beautiful 4-bedroom home pairs comfortable country living with a thoughtfully arranged estate. Set on over 12 pristine acres in Chesapeake, zoned for Hickory schools, this property is a rare rural sanctuary. A wraparound porch welcomes you inside to 9' ceilings, 8' doors, and reclaimed knotty pine floors. The living room features a stone fireplace, opening to a bright kitchen with soft-close cabinets, Samsung Bespoke appliances, and butler’s pantry. Outside, enjoy a saltwater pool, fire pit, and private porches within a completely fenced in yard. The farm boasts a 6-stall barn with wash station, hot water, and mini-split, plus 5 watered pastures, 3 run-ins, and a 50x42 Morton building. An additional 1.5 acres offers potential for a riding arena or agriculture gardening, while a chicken coop, fruit trees, and berries complete the setting. Enjoy southern Chesapeake's rural character, with conveniences and Route 168 nearby.

1713 Sanderson Road, South Chesapeake

$849,900

4 Beds ⋅ 3 Baths ⋅ 10655045 MLS

Welcome to The Ashford by Wetherington Homes -Move-In Ready! A 5-bedroom, 3-bath new construction home with over 2,700 sqft on approximately 2 acres in Hickory School District with NO HOA! Designed for todays buyer, this open-concept floorplan offers luxury finishes, designer details, outdoor entertaining, & flexible living spaces. The kitchen features quartz countertops, Frigidaire Professional appliances, custom wood hood, shaker cabinetry, & upgraded lighting. The 1st floor Primary Suite includes a tiled spa-style shower, dual vanities, & oversized walk-in closet. Two additional 1st floor bedrooms offer flexibility for guests or office space. Upstairs includes 2 bedrooms, full bath, & loft ideal for media room, playroom, or gym. Enjoy luxury new construction convenient to Edinburgh, Greenbrier, shopping, dining, & commuter routes while still offering privacy & acreage!

435 Gallbush Road, South Chesapeake

$575,000

4 Beds ⋅ 3.1 Baths ⋅ 10654917 MLS

This Home is a must to see this beautiful cape style with fruit trees in your own backyard, all sitting on an extra large corner lot, located at Kemp Meadow Dr & Kemp Meadow Way . This home has a downstairs converted garage with a full bathroom. And, both up-down stairs, has great spaces for offices, homeschooling, media room, or whatever your space needs are. The kitchen has attractive counters and many cabinets with upgraded cabinetry, stainless steel appliances. All flooring is either wood, LVP or ceramic tile.

835 Kemp Meadow Drive, South Chesapeake

$550,000

4 Beds ⋅ 2 Baths ⋅ 10654471 MLS

Beautiful Cape Cod ranch on a cul-de-sac lot featuring 4 bedrooms, 2 full baths, and a 2-car side-load garage. The spacious primary suite offers a walk-in closet and bright private bath with dual sinks and skylights, The great room features a gas fireplace, built-in bookshelves, and newer carpet, Convenient main-level bedroom, The kitchen boasts newer LVP flooring and stainless-steel appliances, with French doors leading to a screened-in back porch with ceiling fan. Freshly pressure washed and landscaped, the home offers easy-care yards with irrigation front and back. A backyard shed provides additional storage.

708 Wimbley Lane, South Chesapeake

$625,000

5 Beds ⋅ 3.1 Baths ⋅ 10654210 MLS

Space, space and more space! With over 3,600 square feet, this HOME gives you room to spread out, work, gather and entertain. Hardwood floors flow throughout the majority of the home, while the spacious kitchen features granite countertops and stainless steel appliances. Do you work remotely? There’s a private first-floor office, too. Outside, enjoy an in-ground saltwater pool, Trex deck and gazebo for pool days, cookouts and relaxing at home. And there’s more—the detached garage is ideal for a workshop, hobby space, teen retreat or extra storage. Pool, detached garage, first-floor office, cul-de-sac and no HOA—all wrapped into one very spacious home. If space and flexibility are at the top of your list, this one deserves a look!

803 Gresham Way, South Chesapeake

$415,000

4 Beds ⋅ 2 Baths ⋅ 10654279 MLS

Welcome home to peaceful country living on approximately 0.71 acres! This inviting ranch-style home offers 4 bedrooms and 2 full bathrooms, with fresh paint throughout, new LVP flooring, and new carpet making it move-in ready. The spacious living room features vaulted ceilings, while the kitchen opens to a cozy breakfast nook perfect for morning coffee or casual meals. Out back, enjoy a private yard surrounded by wooded views, an ideal setting for relaxing, entertaining, or simply enjoying a little extra peace and quiet. Tucked away in a country setting yet conveniently located just off Highway 17, this home gives you the best of both worlds: room to breathe with easy access to everything you need.

5144 Ballahack Road, South Chesapeake

$879,900

4 Beds ⋅ 2.1 Baths ⋅ 10654253 MLS

The perfect farmhouse that’s a mix of privacy and closeness to local amenities. Sitting on approx 3 acres in Albemarle Farms, this home offers the updates you've been looking for. Step inside to a bright, welcoming interior with engineered hardwood floors, fresh paint throughout, new trim, and a beautifully updated kitchen. Completed in 2025, the kitchen features all-new cabinetry, quartz countertops, a large island, white stone backsplash, new appliances, and a new sink and faucet. Just beyond, the great room is centered around a new stone fireplace and mantle, while the 4-season room offers a flexible space to relax, work, or enjoy views of the property. Upstairs, the primary suite features a soaking tub and walk-in shower, with two additional bedrooms and bonus space offering plenty of flexibility. Major improvements include new heating and cooling units, new ductwork upstairs and downstairs, a new tankless water heater, and new downstairs subfloor. Outside is where this property really shines, with a saltwater in-ground pool, expansive deck, covered rear porch, circular driveway, and plenty of room to enjoy the wooded setting. An oversized garage with a finished room above adds even more usable space. Located in the Hickory school district with no HOA, this is a home with room to settle in, spread out, and enjoy both indoors and out. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

609 Fairfield Drive, South Chesapeake

$839,900

4 Beds ⋅ 3 Baths ⋅ 10654135 MLS

Interior pics coming!! Welcome to the Hickory lifestyle, where space, privacy, & possibilities come together on 3 acres! This 4-bedroom, 3-bath home offers 2,912 square feet of comfortable living space & plenty of room to enjoy the outdoors. The kitchen features granite countertops & opens to the family room, creating an easy gathering space for everyday life. A formal living room & additional space provide room for an office, playroom, library, or whatever fits your needs. Upstairs, all four bedrooms are generously sized, including a spacious primary suite with a large bathroom featuring a separate walk-in shower & soaking tub & 2 walk-in closets! Outside, the in-ground pool sets the stage for relaxing afternoons at home. And with 3 acres to call your own, there’s room to dream—whether that means a vegetable garden, chickens, outdoor hobbies, or simply enjoying the extra elbow room that makes Hickory living so desirable. Come see all this home & its expansive setting has to offer!

1733 Head Of River Road, South Chesapeake

$599,900

6 Beds ⋅ 3 Baths ⋅ 10654192 MLS

Rare 6-bedroom home with 1st-floor bedroom, adjacent flex room and modified curbless shower—excellent multigenerational potential. Approx. 3,000 SF with 9' ceilings, hardwood floors, large FROG and 2nd-floor laundry. Roof approx. 17 yrs. 2nd-floor HVAC approx. 3 yrs; 1st-floor HVAC approx. 8 yrs. Tankless hot water system. Annual Miller service agreement includes yearly tankless flush. Refrigerator & range less than 1 yr; dishwasher & microwave approx. 3 yrs. Annual termite/moisture contract. Large fenced backyard with room for a pool, detached shed, private irrigation well & attached 2-car garage. Convenient to schools, Veterans Bridge, shopping & commuting routes.

1816 Sunsprite Loop, South Chesapeake

$1,100,000

4 Beds ⋅ 2.1 Baths ⋅ 10653479 MLS

Three wooded acres. A saltwater pool. Five garage bays. Room for the boat, RV and workshop. And no HOA. 1741 Taft Road offers a combination that’s increasingly hard to find in Southern Chesapeake. The approx. 3,700-sq.-ft. home features 4 bedrooms, 2.5 baths and a welcoming wraparound porch. Inside, the kitchen is equipped with matte white Café appliances including a gas range, while the spacious living room centers around a wood-burning fireplace. Upstairs are 4 generously sized bedrooms, including a primary suite with 2 walk-in closets. A finished third floor adds 2 large bonus rooms, creating flexible space for a nursery, home office, gym, studio or private retreat. Outside, an approx. 32,000-gallon saltwater pool and composite deck anchor the backyard, with major pool components updated in 2025–26. A heated 2-car attached garage is joined by a 3-bay detached garage/workshop with propane heat plus mini-split heating and cooling. Covered paved storage accommodates a boat, camper or RV, with a pole barn and additional storage shed adding even more versatility. The acreage continues beyond the rear gate into the woods, where walking trails extend the ways to enjoy the property. Extensive paved parking and a private setting complete a property that offers breathing room without giving up convenient access to Chesapeake.

1741 Taft Road, South Chesapeake

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